Hydrochloric Acid → HCID 68466412, compound

HRID 506776Notes

Reaction equation

HRID 506776 reaction equation
C([O-])([O-])=O.[K+].[K+].I[CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[N:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([C:23]2[N:31]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:26]3=[N:27][CH:28]=[CH:29][CH:30]=[C:25]3[CH:24]=2)=[CH:11]1.[CH3:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1.Cl>CC#N>[CH3:22][O:21][C:15]1[N:14]=[C:13]2[C:12]([C:23]3[N:31]([S:32]([C:35]4[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=4)(=[O:33])=[O:34])[C:26]4=[N:27][CH:28]=[CH:29][CH:30]=[C:25]4[CH:24]=3)=[CH:11][N:10]([CH2:9][CH2:8][N:46]3[CH2:47][CH2:48][N:43]([CH3:42])[CH2:44][CH2:45]3)[C:18]2=[CH:17][C:16]=1[O:19][CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2×HCID 531671-Methylpiperazine2×HCID 68469185HCID 68469185, compound

Product 1

HCID 68466412HCID 68466412, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Add K2CO3 (1.1 equiv., 13.2 mg, 0.095 mmol) to bisazaindole iodide 18 (52 mg, 0.0862 mmol) in CH3CN (6.0 mL) at 60° C., then add 1-methylpiperazine (1.10 equiv., 9.515 mg, 10.55 μL, 0.095 mmol). After stirring for 2 h at 60° C., add extra K2CO3 (13.2 mg) and 1-methylpiperazine (21 μL) and continue stirring at 60° C. for 30 h. The reaction mixture is then concentrated to give a residue, which is treated with 2N HCl and washed with CH2Cl2. The aqueous phase is then treated with 2N NaOH until pH>10 and extracted with CH2Cl2, dried (MgSO4) and concentrated under vacuum, to give 21 (10 mg, 20.2%) as an ivory-colored solid: 1H NMR (CDCl3) δ 8.35 (dd, 1H, J=4.4, 1.1 Hz), 7.72 (dd, 1H, J=4.4, 1.1 Hz), 7.67 (d, 2H, J=8.4 Hz), 7.60 (s, 1H), 7.15 (m, 2H), 7.03 (d, 2H, J=8.4 Hz), 6.98 (s, 1H), 5.28 (s, 3H), 4.26 (t, 2H), 4.00 (s, 3H), 3.97 (s, 3H), 2.86 (t, 2H), 2.55 (m broad, 8H), 2.30 (s, 3H). TLC (MeOH at 10%/CH2Cl2, 0.25% of NH3) Rf=0.35, m/z obs.=575 (M+1).

Workup

  1. stirringcontinue stirring at 60° C. for 30 h
  2. concentrationThe reaction mixture is then concentrated
  3. customto give a residue, which
  4. washwashed with CH2Cl2
  5. additionThe aqueous phase is then treated with 2N NaOH until pH>10
  6. extractionextracted with CH2Cl2
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6f6174a403644612a1c856be25a6b69a
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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